EP0056958A1 - Esters O-quinoleyl-O-alkyl thiono (thiol) phosphoriques(phosphoniques), pesticides les contenant, procédé pour les préparer et leur utilisation - Google Patents

Esters O-quinoleyl-O-alkyl thiono (thiol) phosphoriques(phosphoniques), pesticides les contenant, procédé pour les préparer et leur utilisation Download PDF

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Publication number
EP0056958A1
EP0056958A1 EP82100250A EP82100250A EP0056958A1 EP 0056958 A1 EP0056958 A1 EP 0056958A1 EP 82100250 A EP82100250 A EP 82100250A EP 82100250 A EP82100250 A EP 82100250A EP 0056958 A1 EP0056958 A1 EP 0056958A1
Authority
EP
European Patent Office
Prior art keywords
spp
alkyl
formula
ethyl
thiono
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP82100250A
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German (de)
English (en)
Inventor
Gerhard Dr. Schrader
Ingeborg Dr. Hammann
Bernhard Dr. Homeyer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0056958A1 publication Critical patent/EP0056958A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/60—Quinoline or hydrogenated quinoline ring systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals

Definitions

  • the invention relates to new O-quinolin-3-yl-O-alkylthiono (thiol) -phosphorus (phosphonic) acid esters, a process for their preparation, pesticides containing them, their preparation and use as pesticides, in particular as insecticides and acaricides .
  • O- (4-methyl-quinolin-2-yl) -O-alkylthionophosphorus (phosphonic) acid esters e.g. 0- (4-methyl-quinolin-2-yl) -0,0-diethyl-thionophosphoric acid esters and 0- (4-methyl-quinolin-2-yl) -O-ethyl-thionobenzene phosphonic acid esters can be used to control arthropods can (see German Offenlegungsschrift 1 670 823).
  • insecticidal and acaricidal activity of the known compounds is not always satisfactory, especially when the active substance concentrations are low and the amounts are applied.
  • the new O-quinolin-3-yl-O-alkyl-thiono (thiol) -phosphorus (phosphonic) acid esters of the formula (I) are notable for high activity against animal pests, in particular for high insecticidal and acaricidal activity.
  • the compounds of the formula (I) according to the invention show considerably higher insecticidal and acaricidal activity than corresponding known compounds.
  • Alkyl R and R 1 and alkoxy and alkylthio R 1 can carry one or more, preferably 1 to 3, in particular 1 or 2 identical or different substituents, as are usually found in insecticidal and acaricidal phosphorus derivatives. Examples include: halogens such as fluorine, chlorine and bromine, cyano and alkoxy and alkylthio with preferably 1 to 5, in particular 1 to 3, carbon atoms.
  • the radicals R and R 1 are preferably unsubstituted and each contain 1 to 5, in particular 1 to 3, carbon atoms, it being possible for the alkyl radicals to be straight-chain or branched.
  • R is particularly preferably methyl or ethyl and R 1 is methyl, ethyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio and n- or i-propylthio.
  • R is ethyl and R is ethyl, ethoxy or n-propylthio.
  • the 3-hydroxyquinoline to be used as starting material in the process according to the invention is already known (see J.Org.Chem. 18 (1953), 552).
  • Formula (III) defines the 0-alkylthiono (thiol) -phosphor (phosphon) acid ester chlorides to be used as starting materials.
  • the radicals R and R 1 preferably have the meaning given above as preferred in the definition of these radicals for the compounds of the formula (I).
  • the compounds of the formula (III) are known or can be prepared by generally known processes (see Methods of Organic Chemistry (Houben-Weyl-Müller), 4th edition, volume 12/1 (1963), pp. 560-563 ; Volume 12/2 (1964), pp. 607 - 618; Thieme-Verlag, Stuttgart).
  • diluents Practically all inert organic solvents can be used as diluents. These include in particular aliphatic and aromatic, optionally halogenated hydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl and Dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl, methyl isopropyl and methyl isobutyl ketone, esters such as methyl acetate and ethyl a
  • Acid binders can be used as acid acceptors.
  • Alkali carbonates and alcoholates such as sodium and potassium carbonate, sodium and potassium methylate or ethylate, and also aliphatic, aromatic or heterocyclic amines, for example triethylamine, trimethylamine, dimethylaniline, dimethylbenzylamine and pyridine, have proven particularly useful.
  • the reaction temperature can be varied within a wide range. Generally one works between 0 and 150 ° C, preferably between 10 and 100 ° C.
  • the process according to the invention is generally carried out at normal pressure.
  • the starting materials are usually used in approximately equimolar amounts. A larger excess of one or the other reaction component has no significant advantages.
  • the reaction is generally carried out in a suitable diluent in the presence of an acid acceptor and the reaction mixture is advantageously stirred for several hours at the required temperature.
  • an organic solvent e.g. Methylene chloride and works up the organic phase as usual by washing, drying and distilling off the solvent.
  • the new compounds are obtained in the form of oils, some of which cannot be distilled without decomposing, but by so-called “distillation", i.e. can be freed from the last volatile constituents by prolonged heating under reduced pressure to moderately elevated temperatures and can be cleaned in this way.
  • the refractive index is used to characterize them.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active substance-impregnated natural and synthetic substances, very fine encapsulations in polymeric substances and in coating compositions for seeds, and also in formulations with fuel sets, such as smoking cartridges, cans, spirals, etc., as well as ULV cold and warm mist formulations.
  • customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active substance-impregnated natural and synthetic substances, very fine encapsulations in polymeric substances and in coating compositions for seeds, and also in formulations with fuel sets, such as smoking cartridges, cans, spirals, etc., as well as ULV cold and warm mist formulations.
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • liquid solvents aromatics, such as xylene, toluene, or alkylnaphthalene, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water;
  • Liquefied gaseous extenders or carriers mean those liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellant, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide;
  • Solid carrier materials are suitable: for example natural rock powders such as ka
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular and latex-shaped polymers, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulations.
  • dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can wax in their commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides regulating substances or herbicides.
  • Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and others
  • the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 100% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • the active ingredients When used against hygiene pests and pests of stored products, the active ingredients are distinguished by an excellent residual action on wood and clay and by a good stability to alkali on limed substrates.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves (Brassica oleracea) are treated by dipping into the active compound preparation of the desired concentrations and populated with caterpillars of the owl butterfly (Laphygma frugiperda) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves (Brassica oleracea), which are heavily infested with peach aphids (Myzus persicae), are treated by being dipped into the preparation of active compound of the desired concentration.
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier and the concentrate is diluted with water to the desired concentration.
  • Bean plants Phaseolus vulgaris
  • Bean plants which are severely affected by all stages of development of the common spider mite or bean spider mite (Tetranychus urticae)
  • the kill is determined in%. 100% means that all spider mites have been killed; O% means that no spider mites have been killed.
  • Test insect Phorbia antiqua maggots in the soil
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • the active ingredient preparation is intimately mixed with the soil.
  • test animals After 24 hours, the test animals are placed in the treated soil and after a further 2 to 7 days, the effectiveness of the active ingredient is determined in% by counting the dead and living test insects. The efficiency is 100% if all test insects have been killed, it is 0% if as many test insects are still alive as in the untreated control.
  • the compounds of Examples 1 and 2 have an efficiency of 100% at a concentration of 20 ppm.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Organic Chemistry (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP82100250A 1981-01-27 1982-01-15 Esters O-quinoleyl-O-alkyl thiono (thiol) phosphoriques(phosphoniques), pesticides les contenant, procédé pour les préparer et leur utilisation Withdrawn EP0056958A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19813102519 DE3102519A1 (de) 1981-01-27 1981-01-27 0-chinolin-0-alkyl-thiono(thiol)-phosphor(phosphon)-saeureester, sie enthaltende schaedlingsbekaempfungsmittel, verfahren zu ihrer herstellung und ihre verwendung
DE3102519 1981-01-27

Publications (1)

Publication Number Publication Date
EP0056958A1 true EP0056958A1 (fr) 1982-08-04

Family

ID=6123369

Family Applications (1)

Application Number Title Priority Date Filing Date
EP82100250A Withdrawn EP0056958A1 (fr) 1981-01-27 1982-01-15 Esters O-quinoleyl-O-alkyl thiono (thiol) phosphoriques(phosphoniques), pesticides les contenant, procédé pour les préparer et leur utilisation

Country Status (8)

Country Link
EP (1) EP0056958A1 (fr)
JP (1) JPS57142994A (fr)
AU (1) AU7988882A (fr)
BR (1) BR8200429A (fr)
DE (1) DE3102519A1 (fr)
DK (1) DK34282A (fr)
IL (1) IL64858A0 (fr)
ZA (1) ZA82497B (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE883901C (de) * 1950-06-02 1953-07-23 Hoffmann La Roche Verfahren zur Herstellung von Chinolyl-3-dialkylphosphaten und deren Salzen
DE1670823A1 (de) * 1967-03-20 1971-04-01 Bayer Ag Verfahren zur Herstellung von Phosphor-,Phosphon- bzw. Thionphosphor-(phosphon)-saeureestern

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE883901C (de) * 1950-06-02 1953-07-23 Hoffmann La Roche Verfahren zur Herstellung von Chinolyl-3-dialkylphosphaten und deren Salzen
DE1670823A1 (de) * 1967-03-20 1971-04-01 Bayer Ag Verfahren zur Herstellung von Phosphor-,Phosphon- bzw. Thionphosphor-(phosphon)-saeureestern

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Band 85, No. 5, 2. August 1976, Zusammenfassung 29393w, seite 101 Columbus, Ohio (US) & Phytochemistry 1976, 15(1) 29-31. TANIGUCHI MAKOTO u.a: "Increase of Auxin-Antagonistic Action in 3-Phosphoryloxycarbostyrils" *die ganze Zusammenfassung * *

Also Published As

Publication number Publication date
DE3102519A1 (de) 1982-09-02
IL64858A0 (en) 1982-03-31
DK34282A (da) 1982-07-28
BR8200429A (pt) 1982-11-30
ZA82497B (en) 1982-12-29
JPS57142994A (en) 1982-09-03
AU7988882A (en) 1982-08-05

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PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

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RIN1 Information on inventor provided before grant (corrected)

Inventor name: HAMMANN, INGEBORG, DR.

Inventor name: HOMEYER, BERNHARD, DR.

Inventor name: SCHRADER, GERHARD, DR.